Kent County Public Schools Homes under $500,000

Kent County Public Schools Homes under $500,000

Welcome to Kent County, Maryland, where excellent education meets charming community living! Nestled along the picturesque shores of the Chesapeake Bay, Kent County is home to the highly regarded Kent County Public Schools. Renowned for their commitment to academic excellence, these schools provide a nurturing environment for students from kindergarten through high school. With a focus on personalized learning and innovative teaching methods, Kent County Public Schools ensure that every child receives the support and resources they need to thrive.

Families moving to this beautiful area will find an impressive selection of homes priced under $500,000. Whether you’re seeking a cozy cottage, a spacious family home, or a charming historic residence, Kent County has something for everyone. The real estate market offers a diverse range of options, allowing you to find the perfect home that fits your lifestyle and budget.

Kent County’s idyllic surroundings make it an ideal place for families to grow and flourish. With access to outdoor activities, scenic parks, and vibrant local culture, residents enjoy a balanced lifestyle filled with adventure and relaxation. The community spirit is palpable, with numerous events and activities that bring neighbors together, fostering lasting friendships.

Choosing Kent County means investing in a community that values education, quality living, and a strong sense of belonging. Explore the homes available under $500,000 and discover why so many families are proud to call Kent County home. Your dream home awaits in this charming corner of Maryland!

Newest Kent County Public Schools Homes under $500,000

206 N Mill St, Chestertown
$430,000
3 Beds ⋅ 3 Baths
Welcome to 206 North Mill Street. This spacious three-bedroom Victorian - set on a quiet, dead-end street - is just a few steps from everything downtown Chestertown has to offer. Timeless interior features include solid hardwood floor throughout all three floors, baseboard and crown molding, brick fireplace, marble countertops and much more. This home is great for everyday living or a weekend retreat. Enjoy easy summer evenings on the lovely front porch. Inside you are greeted by a large family room in front with a brick fireplace featuring a wonderful built-in wooden mantel surround. Moving back, the spacious kitchen has lots of of cabinets and countertop space with overhanging bar seating and a breakfast and dining space behind. A half bath and laundry room in the back complete the first floor. Moving upstairs, you will find the large primary suite with his and her closets and ensuite bath. A generously sized 2nd bedroom and shared full bath complete the second floor. The private 3rd bedroom on the third floor finishes the interior. Mature trees provide lots of shade and privacy in the private back yard with garden shed. Dual zoned heat pumps for heating and air. Dedicated parking on right side of street. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market, and a laid-back lifestyle with an endless number of social or volunteer activities. Less than 90 minutes to Washington D.C. or Philadelphia.

206 N Mill St, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

28036 Creamery St, Kennedyville
$224,900
3 Beds ⋅ 1 Baths
Welcome to 28036 Creamery Street in Kennedyville. Built in 1920, this two-story home offers 3 bedrooms, 1 full bath and 1,296 square feet of living space, along with two parcels totaling approximately .224 acre. The main level features a large kitchen with a sightline into the dining room, living room, full bath, and a convenient laundry/utility area located just off the dining room. All three bedrooms are located on the upper level. The home is functional and ready for its next owner, while also offering an opportunity for buyers who would like to make improvements and updates over time to suit their own style. The sale includes the .109-acre homesite plus an adjoining .115-acre parcel, providing additional outdoor space and possibilities. Located in the Eastern Shore community of Kennedyville, the property is a short drive to historic Chestertown for shopping, dining and everyday conveniences. Enjoy access to the area's outdoor recreation, including the Sassafras River, Turner's Creek and Sassafras Natural Resources Management Area, with opportunities for boating, fishing, kayaking and hiking. Betterton and Rock Hall provide additional Chesapeake Bay destinations within the surrounding area. Routes 213 and 301 also provides connections toward Middletown, Dover and surrounding employment and shopping areas. Property is being sold As-Is.

28036 Creamery St, Kennedyville

Listing courtesy of BHHS Fox & Roach-Christiana. Contact:

234 N Kent St, Chestertown
$325,000
5 Beds ⋅ 2 Baths
Some houses are finished. This one is full of opportunity. Built circa 1920, this Victorian sits in one of Downtown Chestertown's most desirable neighborhoods — and it's waiting for someone who can see what it is meant to become. The hard work and the expensive work have already been done: new cedar siding, blown-in insulation, and original hardwood floors throughout. What remains is the fun part. The kitchen and baths are a genuine blank slate, ready for your design, your finishes, your vision. And the bones… remarkable. Solid construction, generous proportions, and historic detail at every turn — the kind of craftsmanship that simply isn't built anymore, and can't be bought back once it's gone. Start with a house of real character and your renovation adds value instead of merely keeping up. Upstairs, five generous bedroom and two full baths. A rare third-floor primary suite offers space and privacy set apart from the rest of the home — a true owner's retreat, a guest wing, or a quiet work-from-home floor of its own. Outside, a fully fenced backyard is ready for pets, play, and entertaining, a large shed could easily become a garage, studio, or workshop. The driveway provides off-street parking, a definite bonus for Chestertown. And the location is the whole point. You're roughly three blocks from everything Chestertown offers — the shops, restaurants and galleries along High Street, the Chester River waterfront, the farmers market, and the historic charm of one of the Eastern Shore's best-loved small towns. Bring your contractor, or be your own. Come see the possibility.

234 N Kent St, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

8820 Cumberland St, Chestertown
$312,500
3 Beds ⋅ 2 Baths
Discover relaxed Eastern Shore living at 8820 Cumberland Street, a charming three-bedroom, two-full-bath home offering the ease and convenience of single-level living in the peaceful water-privileged community of Tolchester Beach. Built in 2006, this inviting residence combines a comfortable floor plan, desirable outdoor space, and an attached two-car garage with a setting that encourages you to slow down and enjoy the best of Maryland's Eastern Shore. The thoughtfully designed interior provides an easy flow for everyday living, with three well-proportioned bedrooms and two full baths all conveniently located on one level. Whether you're entertaining, working from home, or simply enjoying a quiet evening, the home's practical layout offers flexibility for a variety of lifestyles. Step outside to the rear deck, where a wooded backdrop creates a tranquil setting for morning coffee, outdoor dining, or relaxing at the end of the day. The surrounding natural scenery adds a welcome sense of privacy and peacefulness. The community's water-oriented amenities add to the appeal, with opportunities to enjoy the community beach, fishing, local marina, and the laid-back lifestyle that makes the Eastern Shore so desirable. Ideally positioned between historic Chestertown and waterfront Rock Hall, the home places shopping, dining, marinas, boating, and local recreation within convenient reach. Whether you're seeking a full-time residence, weekend retreat, or low-maintenance Eastern Shore escape, 8820 Cumberland Street offers an appealing blend of comfort, convenience, and coastal lifestyle. This property is being sold as-is, property is lender-owned and U.S. Bank National Association is making no representations or warranties. U.S. Bank National Association may have financing options available.

8820 Cumberland St, Chestertown

Listing courtesy of RE/MAX Advantage Realty. Contact:

103 Metcalf Rd, Chestertown
$259,900
3 Beds ⋅ 3 Baths
Ask about our SELLER-PAID RATE BUYDOWN — the builder is paying to permanently lower your interest rate when you finance with our preferred lender, who is also contributing toward your closing costs. The result: a dramatically lower monthly payment on a brand-new home, saving you well over a hundred dollars every month — even more on lower-down-payment financing. This is real payment relief in today's market — often the difference between watching and owning. Brand-new construction in the heart of Chestertown. Buydown applies with use of preferred lender; see agent for details. Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown’s most historic locations. Ask about Special Financing Offers and how to get $7,500 or more in closing help from the builder's preferred lender and on select models, while they last!

103 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact:

14 Third Ave, Betterton
$245,000
3 Beds ⋅ 3 Baths
A rare opportunity near the Chesapeake Bay! Bring your vision to life in the charming waterfront community of Betterton. This Victorian-style home offers over 2,068 sq. ft., featuring a completed exterior and an unfinished interior that gives the next owner the opportunity to finish and customize the home to their own style. Designed for 3 bedrooms and 3 full bathrooms, with the potential for a 4th bedroom or additional living space above the garage. The unfinished interior features open stud walls with roughed-in plumbing and electric, underground electric with 200-amp service, 2x6 exterior walls, 9-foot ceilings on the first floor and basement, Andersen windows, steel entry doors, and an oversized garage door. A beautiful wrap-around porch, attached side-entry garage, and cleared, level 0.24-acre lot add to the possibilities. Located just 3 short blocks from the Chesapeake Bay and a short walk to Betterton Beach, enjoy convenient access to the beach, boardwalk, boat ramp, fishing, swimming, basketball and tennis courts, picnic pavilions, and a town playground. Whether you're envisioning a year-round residence, vacation getaway, or investment opportunity, much of the vision is already in place. Bring your ideas and make this unique property near the Bay your own!

14 Third Ave, Betterton

Listing courtesy of Foraker Realty Co.. Contact:

14 1st Ave, Betterton
$410,000
4 Beds ⋅ 2 Baths
Welcome 14 1st Avenue - a charming Victorian just steps from the Betterton bluff and public beach and with water views from the back deck and primary bedroom. Known as the Jewel of the Chesapeake, Betterton is located at the confluence of the Sassafras River and Chesapeake Bay and got its reputation for its picturesque sunsets and wonderful public beach. Embrace the waterfront lifestyle and so much more without the waterfront taxes. This four bedroom, two full bathroom home has been lovingly maintained and is full of historic charm: hardwood floors throughout both levels, crown, baseboard, and bullseye moldings, transom windows, the list goes on. Brand new architectural shingle roof in 2025. Geothermal heating and cooling systems are energy efficient and cost effective. The first floor layout is all about convenience with an open layout and full bath. Natural light abounds the living, dining and kitchen spaces. Moving upstairs you will love the spacious primary bedroom with vaulted ceiling and water views out the back window. A full bath, three more bedrooms and a large attic / storage space complete the second floor. Large walkout basement providing easy access for bikes, kayaks, paddle boards, you name it! Just a few steps from the water with excellent southern exposure as well. This is the perfect weekend getaway or primary residence on the Eastern shore. Come see all that the Jewel of the Chesapeake has to offer.

14 1st Ave, Betterton

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

331 Devon Dr, Chestertown
$499,999
4 Beds ⋅ 4 Baths
Welcome to 331 Devon Drive in Family friendly Coventry Farms. With 4 bedrooms and 3.5 bathrooms, this recently updated and meticulously maintained Colonial home offers enough space for the whole family and a harmonious blend of convenience and elegant living. The owners have an assumable VA Mortgage below 4.5% The well-designed first floor - featuring tall ceilings, new dimmable recessed lighting and a wood burning fireplace - is anchored by the open-concept kitchen and living room spaces, which flow naturally to the exterior deck. The upgraded gourmet kitchen is a chef's dream, featuring upgraded countertops, stainless steel appliances, and a spacious island that invites culinary creativity. The kitchen flows effortlessly into the family room, where a cozy fireplace serves as the focal point, perfect for gathering with loved ones. The back of the house flows easily through sliding glass doors to the large back deck overlooking a large community open space with trees and a rolling field. A formal dining room off the kitchen and a large office space complete the first floor. Moving upstairs, there is brand new carpet throughout all four bedrooms. The master suite is a true retreat, complete with a walk-in closet and an en-suite bathroom. The attached garage accommodates two vehicles, while the paved driveway provides additional parking for guests. An electric vehicle charging station is great for those with an EV. The finished walkout basement with a full bathroom is a large open space offering possibilities for a second living room, home gym, entertainment area, etc. A Sunrun Solar system has significantly reduced the home's electric bill. Recent upgrades include: GE Profile SS kitchen appliances, deep farm-style sink, Trane heating / air air system, recessed lighting, fans, second floor carpet, interior and exterior paint throughout and more. Coventry Farms is just a couple minutes from downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront parks. Home to many festivals, an award-winning weekly Farmer's Market, Chestertown has a laid-back lifestyle with an endless number of social or volunteer activities. Less than 90 minutes to Washington D.C. or Philadelphia. Enjoy country living on the Eastern Shore. More photos and information to come!

331 Devon Dr, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

5855 Cottage Ave, Rock Hall
$425,000
3 Beds ⋅ 3 Baths
NEW CONSTRUCTION in the charming Eastern Shore town of Rock Hall! This beautiful Colonial-style home offers the perfect blend of modern construction, comfortable living, and small-town Eastern Shore charm. Featuring 3 bedrooms, 2 full baths, and 1 half bath, this thoughtfully designed home boasts an inviting open floor plan that creates an easy flow between the living, dining, and kitchen areas. Step inside from the cozy front porch and appreciate the quality and efficiency built into this home. Energy-conscious features include high-efficiency windows and doors, quality insulation, and a professionally conditioned, watertight crawl space designed to provide a cleaner, drier, more efficient foundation for years to come. For added convenience, laundry is located on the top floor, making everyday living and household chores that much easier. Parking is plentiful, with a spacious driveway in the front as well as convenient additional access from the side entrance off Cottage Street. Situated on a large lot, there is plenty of room to enjoy the outdoors and even the potential to add an approximately 1,200-square-foot outbuilding—perfect for a workshop, garage, storage, studio, or other future needs (subject to applicable approvals and zoning). Located in the wonderful waterfront community of Rock Hall, Maryland, you'll be close to the area's marinas, restaurants, shops, and the Chesapeake Bay while enjoying the relaxed lifestyle that makes Rock Hall such a special Eastern Shore destination. Coming to market October 1st — don't miss your opportunity to tour this beautiful new home!

5855 Cottage Ave, Rock Hall

Listing courtesy of RE/MAX Point Realty. Contact:

25094 Reeds Mdw, Worton
$389,000
3 Beds ⋅ 3 Baths
Nestled in the community of Reeds Meadows, this contemporary residence offers a blend of modern convenience and comfortable living. Built in 2020, this meticulously maintained home spans 1,974 square feet, providing ample space for relaxation and entertainment. As you approach the property, you are greeted by a charming exterior with durable vinyl siding, complemented by well-maintained entry. The newly paved road invites leisurely strolls in a pleasant setting. An asphalt driveway leads to an attached garage featuring convenient inside access as well as access to the rear of the property. A garage door with remote opener ensures effortless entry and exit. Step inside to discover a thoughtfully designed layout that emphasizes both functionality and style. The heart of the home is the kitchen, equipped with stainless appliances including a built-in microwave, sleek dishwasher, and a classic range hood. The new refrigerator and stove make meal preparation a delight, while the adjacent laundry area with half bath is conveniently located on the main floor. Natural light pours through large windows, enhancing the warm ambiance throughout. The absence of a fireplace allows for a clean, modern aesthetic, while the contemporary design elements provide a timeless appeal. Retreat to the tranquil first floor master suite, complete with an en-suite bathroom featuring luxurious finishes. Two additional bedrooms, a bonus room, and a well-appointed full-bath ensure comfort and privacy for all. Step outside onto the custom deck, perfect for alfresco dining or simply enjoy the peaceful surroundings of your 0.32-acre lot. This outdoor space is ideal for hosting summer barbecues or unwinding with a good book in the fresh air. Experience the lifestyle that you deserve.  Don't miss the opportunity to make this residence your own. Located about 10 minutes from historic Chestertown on the Chester River, this tidy subdivision 's location offers quick access to public landings for fishing and boating fun, beautiful farms, including Red Acres, which offers beautiful produce, flowers, and retail products. Located between Chestertown/Galena, and Betterton, and also close to Rock Hall which boasts good shopping, restaurants and loads of fun on the Chesapeake Bay.

25094 Reeds Mdw, Worton

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

10 Cedar Chase Ct, Chestertown
$495,000
3 Beds ⋅ 3 Baths
Beautiful waterviews of the Chester River set the stage for this special Chestertown property, located in desirable Mile Tree Village and just a short walk from the Historic District. Set on .53 acres, the home offers 1,656 square feet of finished living space on the main level, with 3 bedrooms and 2 full baths, plus an unfinished lower level with a half bath and one-and-a-half-car garage. An upper-level deck, accessible from the living room, dining room, and primary suite, provides the perfect spot to enjoy the river views and the easy Eastern Shore lifestyle. The home is ready for a fresh vision and offers tremendous potential to become a luxury waterview residence. Thoughtful updating could transform the existing spaces into a home that takes full advantage of the setting. Within a short walk or bike ride to Chestertown's Historic District for dinner, shopping, galleries, and Annual Festivals, while the Chester River provides a beautiful backdrop to everyday life. Bring your vision and create a truly special waterview home and experience the Eastern Shore Lifestyle at its finest!

10 Cedar Chase Ct, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

22974 Bay Shore Rd, Chestertown
$329,900
2 Beds ⋅ 2 Baths
Welcome to this charming farmhouse-style home in Fairlee! Completely renovated in 2023, this home is move-in ready and offers a comfortable mix of modern updates and farmhouse charm. Inside, you’ll find an open floor plan with luxury vinyl plank flooring throughout the main living areas. The living room offers a cozy space to relax and unwind. The updated kitchen is the heart of the home and features beautiful finishes and newer appliances, making it a great space for cooking and gathering. The home features two bedrooms, including a spacious primary bedroom, and two full bathrooms that have both been nicely updated. The spacious laundry room/mudroom provides plenty of room and adds everyday convenience. Enjoy your morning coffee or unwind at the end of the day on the inviting front porch, a great spot to sit back and enjoy the peaceful surroundings. Outside, you’ll find a large half-acre lot that backs to farmland, offering a beautiful setting. There’s plenty of room to enjoy the outdoors, garden, or let the kids and pets play. The gravel driveway provides parking for up to four vehicles. If you’re looking for a home that has been beautifully updated while still keeping that cozy farmhouse feel, this one is worth a look. Come see everything this Fairlee home has to offer!

22974 Bay Shore Rd, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

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